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In this paper, I shall describe the psychoanalytic treatment of a fourteen-year-old boy who suffered from a moderately severe form of Asperger’s syndrome. This adolescent had a multiplicity of imaginary friends, which protected him from catastrophic annihilation anxieties, but at the same time hindered his ability to establish meaningful relationships with human beings. As the relationship with the therapist gradually gained the vitality and importance originally invested in his parallel fantasy world, the imaginary companions simultaneously faded away. His imagination then became more closely connected to inner reality and to creative processes. The psychoanalytic literature on imaginary companions is reviewed, and it is suggested that the concept of a self-protective device could be usefully applied to understanding the functions that this fantasy performed for the patient. The addictive quality of these constructions is also considered, and it is suggested that they offered a “doubtful alliance” against the pains of dependency.